Synthesis of mono-amino-functionalised ferrocene, ferrocene salts and ferrocenium salts

Abstract

A number of mono-amino-functionalised ferrocenes, ferrocene salts and a mono-amino-functionalised ferrocenium salt have been synthesised and characterised. This represents a novel method of accessing these important classes of molecules. In the cases of some of the ferrocene salts, there are some interesting structural features in the solid state. These include N-H...O and N-H...F hydrogen bonds.

The First (Ferrocenylmethyl)imidazolium and (Ferrocenylmethyl)triazolium Room Temperature Ionic Liquids

“…Although we report the first ferrocenyl-containing room-temperature ionic liquids, while this work was in review, new routes to the synthesis of a number of mono-amino-functionalized ferrocenes, ferrocene, and ferrocenium salt counterparts were reported. Structural studies show N−H···O and N−H···F hydrogen bonds . Similar compounds, such as α-(ferrocenylethyl)-1 N -benzo-1,2,3-triazole, have been demonstrated to inhibit tumor growth and increased life expectancy in animals.…”

Synthesis, characterization and antitumor activity of 1,2-disubstituted ferrocenes and cyclodextrin inclusion complexes

“…One approach to improve the water solubility of metallocene anticancer drugs is to prepare the corresponding ionic salts with the charge linked to the cyclopentadienyl ligands. McGowan and co-workers have, for example, prepared several amino-functionalized ferrocene salts [63,64]. We therefore synthesized an ammonium iodide salt 7 by reaction of 5 with CH 3 I.…”

Selective Electrochemical Detection of Hydrogen Fluoride by Ambiphilic Ferrocene Derivatives

“…The structure of 5 has been elucidated from spectroscopic and X‐ray diffraction measurements and reveals—in addition to substitution of the two boronic acid OH groups by fluorine atoms17—the binding of a single equivalent of HF (Figure 3). The residual intramolecular H⋅⋅⋅F interaction is relatively weak, as evidenced by a separation of 2.204 Å (0.92 Å for gaseous HF),18 and is best viewed as an ionic hydrogen bond between the BF 3 − and NMe 2 H + fragments 19. In the solid state these hydrogen‐bonded units are linked through additional intermolecular H⋅⋅⋅F interactions (2.124 Å) into centrosymmetric dimers.…”